4-Methylene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid

Base Information

• Chemical Name: 4-Methylene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid
• CAS No.: 218137-86-1
• Molecular Formula: C₁₄H₂₂O₄
• Molecular Weight: 254.326
• Hs Code.: 2932190090
• UNII: 8E9A8CTX2H
• ChEMBL ID: CHEMBL477382
• DSSTox Substance ID: DTXSID401189534
• Nikkaji Number: J1.840.018I
• Wikidata: Q27166884
• Mol file: 218137-86-1.mol

Synonyms:218137-86-1;C75;4-Methylene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid;C-75;4-methylidene-2-octyl-5-oxooxolane-3-carboxylic acid;FAS inhibitor C75;4-Methylene-2-octyl-5-oxo-tetrahydro-furan-3-carboxylic acid;8E9A8CTX2H;CHEMBL477382;MFCD03426157;tetrahydro-4-methylene-2-octyl-5-oxo-3-furancarboxylic acid;3-Furancarboxylic acid, tetrahydro-4-methylene-2-octyl-5-oxo-;UNII-8E9A8CTX2H;MLS006010729;SCHEMBL360509;CHEBI:95108;CHEBI:191402;DTXSID401189534;C 75;BCP09082;EX-A3806;BDBM50525849;NSC764756;AKOS015911704;C75, >=98% (HPLC), powder;CS-3562;NSC-764756;NCGC00165772-01;NCGC00165772-02;HY-12364;MS-23584;SMR004701691;FT-0675031;FT-0748416;A911804;A925067;Q27166884;4-methylidene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid

Chemical Property of 4-Methylene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid

Chemical Property:

• Vapor Pressure: 1.12E-08mmHg at 25°C
• Refractive Index: 1.488
• Boiling Point: 432.1°C at 760 mmHg
• PKA: 3.08±0.40(Predicted)
• Flash Point: 159.2°C
• PSA: 63.60000
• Density: 1.08g/cm³
• LogP: 2.91940
• Storage Temp.: 2-8°C
• Solubility.: DMSO: 18 mg/mL
• XLogP3: 4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 254.15180918
• Heavy Atom Count: 18
• Complexity: 322

Purity/Quality:

98%,99%, ^*data from raw suppliers

C 75 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCC1C(C(=C)C(=O)O1)C(=O)O
• Uses: C75 has been used:as a fatty acid synthase (FASN) inhibitor to test its ability in the direct inhibition of FASN to attenuate mammosphere formation as compared to metforminas a pharmacological inhibitor to inhibit fatty acid synthesis in glioma stem cells (GSCs)as FAS inhibitor in the pre-treatment of Chang cells to inhibit lipogenesis and reverse the senescence induced by hydrogen peroxide

Technology Process of 4-Methylene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid

There total 23 articles about 4-Methylene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 60.0%

(4R,5R)-4-(hydroxymethyl)-3-methylene-5-octyldihydrofuran-2(3H)-one → C75 (1234694-20-2,1234694-22-4,191282-49-2,191282-48-1,218137-86-1)

Guidance literature:

With Jones reagent; at 0 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/acs.orglett.0c04165

Reference yield: 60.0%

4-(hydroxymethyl)-3-methylene-5-octyldihydrofuran-2(3H)-one → C75 (1234694-20-2,1234694-22-4,191282-49-2,191282-48-1,218137-86-1)

Guidance literature:

With Jones reagent; at 23 ℃; for 0.166667h; Inert atmosphere;

DOI:10.1021/acs.orglett.0c04165

Reference yield: 29.0%

methyl (2S,3R)-4-methylene-5-oxo-2-octyltetrahydrofuran-3-carboxylate (1234694-21-3) → C75 (1234694-20-2,1234694-22-4,191282-49-2,191282-48-1,218137-86-1)

Guidance literature:

With liver acetone powder equine; In aq. phosphate buffer; acetone; for 24h; pH=7.4; enantioselective reaction; Enzymatic reaction;

DOI:10.1002/chir.22419

upstream raw materials:

methyl (2S,3R)-4-methylene-5-oxo-2-octyltetrahydrofuran-3-carboxylate

4-methoxy-2-methylene-4-oxobutanoic acid

nonan-1-al

4-((4-methoxybenzyl)oxy)-2-methylene-4-oxobutanoic acid

Refernces

• 1、 Chakrabarty, Kuheli,Defrenza, Ivana,Denora, Nunzio,Drioli, Sara,Forzato, Cristina,Franco, Massimo,Lentini, Giovanni,Nitti, Patrizia,Pitacco, Giuliana. "Enzymatic resolution of α-methyleneparaconic acids and evaluation of their biological activity". . p. 239 - 246. Retrieved 2015/03/18.
• 2、 -. "INHIBITION OF FATTY ACID SYNTHASE AS A MEANS TO REDUCE ADIPOCYTE MASS". Page/Page column 10; 11. . Retrieved 2010/02/13.